Profile of a NYC pickpocket

Wilfred Rose, a career NYC pickpocket now in prison, claims to be retired. In his decades as a "shotplayer," he became a legend.

He's part of a dying breed -- contemporary thieves are more interested in things like ATM skimming -- and in a long NYT profile, he describes the fascinating tricks of his trade, which included a tactic for increasing the crowds in subway cars by gaming the door-closing intervals and blowing the trains' logistical calculations.

In the jail’s visiting room, Mr. Rose demonstrated his main technique. Placing a thumb on the outside of the pants for leverage, he used a forefinger in an upward scratching motion, showing how he would tug at the pocket lining.

“We call it ‘winding it up.’ It raises the cash,” he said. When the money is accessible, Mr. Rose forms pincers with his middle finger and the back of his forefinger to extract the cash.

Beyond technique, he said, what’s needed is a crowd. Some of his favorite spots include parades along Fifth Avenue and busy subway trains.

If a particular subway train was not crowded enough, he and other pickpockets would manipulate the playing field. Mr. Rose said he and Mr. Simmons would delay southbound trains in Harlem, holding open the doors at the 116th and 110th Street stations. “It would be a two- or three-minute delay, or maybe a bit more,” he said. But that was all it took for the downstream platforms to fill with passengers waiting for the next train to arrive. By the time Mr. Rose rode into the station, they would be packing his car, providing ideal working conditions.

Mr. Rose said he would try to strike before the train reached Times Square or Union Square, where there was a high concentration of transit police officers, particularly those in plain clothes who spend their days looking for pickpockets. Mr. Rose admitted to a fascination with the officers who pursued him, discussing them by name and speaking admiringly of their knowledge of pickpockets.